Overlooking Chianti to one side and the Val d’Orcia to the other, Siena sits in one of the most scenic corners of Tuscany. Most visitors come to marvel at the town itself more than the views, since this medieval hill town has remained virtually unchanged for the past 500 years. Stop to explore its UNESCO-listed historic center, with the shell-shaped Piazza del Campo—ringed by the Palazzo Pubblico town hall, Fontana Gaia fountain, and Torre del Mangia tower—at the center.

Just a bit farther to the south in Tuscany, Pienza overlooks the picturesque hills of the Val d’Orcia. Its elegant old town was planned and constructed by the Renaissance architect Bernardo Rossellino, commissioned by Pius II to give the pope’s hometown a glow-up. Join a local guide to learn more about how this town was completely renovated in the span of just three years, and marvel at Piazza Pio II, home of the Palazzo Piccolomini, Palazzo Borgia, and cathedral.

With its theatrical perch high above the surrounding plains, the medieval town of Orvieto has a unique wow factor. Its soaring cathedral can be spotted from miles away, though the city is also famous for its warren of underground tunnels—some dating as far back as Etruscan times—that are hidden deep beneath the city. One of the most famous towns in the region of Umbria, Orvieto merits a tour to see its Gothic duomo and intact old town, and to taste its excellent white wine.

The historic town of Tivoli is home to two UNESCO World Heritage Sites and an Italian National Heritage Trust gem. Stop here to tour the 16th-century Villa d'Este, famous for its gardens and fountains, or spend an entire day and take in the ancient ruins of Emperor Hadrian's sprawling Villa Adriana estate and the protected woodlands of Parco Villa Gregoriana. Spend some time exploring the town of Tivoli itself, including Via delle Cascatelle.

The rolling Alban Hills of Lazio’s Castelli Romani (or “Roman Castles”) have been a favored retreat for Romans for millennia. Today, this area is thick with storied towns and villages that offer something for everyone: wine lovers can pause in the vineyards outside Frascati for a wine tasting and lunch; history buffs will want to tour the pope’s summer palace in Castel Gandolfo; and outdoor enthusiasts can paddle through the waters of Lake Albano on a kayaking tour.

The largest royal residence in the world, the 18th-century Royal Palace of Caserta impresses with its massive size and sumptuous baroque style. This UNESCO World Heritage Site is one of the most-visited monuments in southern Italy, well worth a stop to explore its palace and park. Built by the architect Luigi Vanvitelli for the Bourbon kings of Naples, it was inspired by the Palace of Versailles in France and has 1,200 rooms on five levels plus gardens and water features.

In 79 AD, the rumbling volcanic peak of Mount Vesuvius blew its top, covering the bustling city of Pompeii in volcanic ash and debris, preserving its shops, villas, temples, and more for almost 2,000 years. Venture into the past with an archaeologist-led tour of these compelling ruins to learn about daily life during the height of the Roman empire, from the construction of the paved roads to the engineering behind the city’s baths and theaters.

Not technically part of the Amalfi Coast but considered by most as the gateway to Italy’s most fashionable stretch of coastline, Sorrento has been a beloved resort retreat since the 18th century. Meander through its old town on a walking tour, browse the shops and enjoy regional specialties from Campania, take in views over the coastline from the Villa Comunale, sip a caffè napolitano in Piazza Tasso, and take your first dip at Marina Grande before continuing along the Sorrentine Peninsula.